Veratraldehyde → 1-(3,4-Dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethylene

HRID 1795490Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:6]P(=O)(OCC)OCC.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:27]=O.[H-].[Na+]>>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:6][C:5]2[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

Reactant 3

HCID 8419Veratraldehyde

HCID 24758Sodium hydride

HCID 10018756Diethyl 3,4,5-trimethoxybenzylphosphonate

Product 1

HCID 3571821-(3,4-Dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethylene

Procedure

Reaction of diethyl 3,4,5-trimethoxybenzylphosphonate (5.4 g, 17 mmol) with 3,4-dimethoxybenzaldehyde (2 g, 12 mmol) in presence of NaH (0.97 g, 20 mmol), under the conditions noted in example 1, gave 1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethylene, m.p. 150–152° C.; IR (KBr) νmax 2934, 2835, 1583, 1510, 1331, 1249, 1125, 1024, 1004, 976, 850 cm−1; 1H NMR (CDCl3, 400 MHz) δ 7.06 (1H, s), 7.05 (1H, dd, J=8.0, 1.9 Hz), 6.97 (1H, d, J=16.0 Hz), 6.89 (1H, d, J=16.0 Hz), 6.87 (1H, d, J=8.0 Hz), 6.73 (2H, s), 3.95 (3H, s), 3.92 (6H, s), 3.91 (3H, s), 3.87 (3H, s).

Sources & evidence

ORD record: ord-4420c2c365214d69a9782ab258fd9eb6
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026518B2

Reaction notes

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